Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Guatemala City, Guatemala: Biz from $807 Econ from $213. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Biz from $437 Econ from $92. – Jul-Sep
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Orlando, Florida: Econ from $65. – Jul-Sep
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Tirana, Albania: Biz from $2313 Econ from $483. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Porto, Portugal: Econ from $440. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Ontario, California: Econ from $98. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Norfolk, Virginia: Biz from $432 Econ from $100. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Punta Cana, Dominican Republic: Econ from $239. – Jun-Aug (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tunis, Tunisia: Biz from $2687 Econ from $801. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Nashville, Tennessee: Biz from $307 Econ from $38. – Jul-Sep (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Thera, Greece: Econ from $654. – Apr-Jun
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Sarajevo, Bosnia and Herzegovina: Econ from $464. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Baltimore, Maryland: Econ from $48. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Montego Bay, Jamaica: Biz from $928 Econ from $253. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Gdansk, Poland: Econ from $532. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Washington, DC: Econ from $96. – Jul-Sep
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Belgrade, Serbia: Econ from $526. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Portland, Oregon: Econ from $107. – Jul-Sep
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Bridgetown, Barbados: Econ from $259. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Raleigh, North Carolina: Biz from $427 Econ from $86. – Jun-Aug (Including Summer Break)
3 different flights to/from Raleigh – All under $100 round-trip. * This is an airline sale that is time-sensitive. Plenty…
ORD > Oslo, Norway: Econ from $489. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Denver, Colorado: Biz from $457 Econ from $54. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Amman, Jordan: Econ from $801. – Sep-Nov (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Medellin, Colombia: Biz from $825 Econ from $229. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Simpson Bay, St. Maarten: Econ from $315. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Madrid, Spain: Econ from $380. – Jan-Mar (Including President’s Day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > New York, New York: Biz from $379 Econ from $101. – Aug-Oct
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Asheville, North Carolina: Econ from $79. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Abuja, Nigeria: Biz from $3391 Econ from $936. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Seattle, Washington: Econ from $173. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Miami, Florida: Econ from $48. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Luqa, Malta: Econ from $532. – Nov-Jan (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Santo Domingo, Dominican Republic: Biz from $822 Econ from $272. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Santiago, Chile: Biz from $1996 Econ from $524. – Jul-Sep
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Warsaw, Poland: Econ from $500. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Atlantic City, New Jersey: Econ from $119. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Knoxville, Tennessee: Biz from $359 Econ from $75. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guayaquil, Ecuador: Biz from $936 Econ from $296. – Aug-Oct
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Guadalajara, Mexico: Biz from $610 Econ from $212. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…